JPS61162507A - Production of copolymer with high heat resistance and good flowability - Google Patents
Production of copolymer with high heat resistance and good flowabilityInfo
- Publication number
- JPS61162507A JPS61162507A JP369085A JP369085A JPS61162507A JP S61162507 A JPS61162507 A JP S61162507A JP 369085 A JP369085 A JP 369085A JP 369085 A JP369085 A JP 369085A JP S61162507 A JPS61162507 A JP S61162507A
- Authority
- JP
- Japan
- Prior art keywords
- copolymer
- parts
- styrene
- heat resistance
- aromatic vinyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Abstract
Description
【発明の詳細な説明】
〈発明の目的〉
本発明は、耐熱性ならびに流動性に優れる芳香族ビニル
ールイミド系共重合体の製造法に関する。DETAILED DESCRIPTION OF THE INVENTION <Object of the Invention> The present invention relates to a method for producing an aromatic vinylulimide copolymer having excellent heat resistance and fluidity.
スチレンモノマーは、熱、光、触媒によって容易に重合
する化合物であり、又、得られるスチレン系樹脂は成形
性、着色性などに優れる汎用樹脂として多方面において
用いられる。Styrene monomers are compounds that are easily polymerized by heat, light, and catalysts, and the resulting styrene-based resins are used in many fields as general-purpose resins with excellent moldability, colorability, etc.
スチレン系樹脂の耐熱性を向上させるための研究が古く
から行われているが、中でもスチレンの一部をα−メチ
ルスチレンに置換してｌるα−メチルスチレン系樹脂が
よく知られている。Research has been conducted for a long time to improve the heat resistance of styrene resins, and among them, α-methylstyrene resins in which a part of styrene is replaced with α-methylstyrene are well known.
しかしながら、α−メチルスチレンモノ１−はスチレン
モノマーに比べ著しく重合性が悪く、１合後多くの未反
応体として残るため工業生産としてはひじように不経済
である。However, α-methylstyrene mono-1- has significantly poorer polymerizability than styrene monomers, and much unreacted material remains after 1-merization, making it very uneconomical for industrial production.
さらに、近年スチレン系樹脂に対する耐熱性の要求はま
すます高くなってきており、α−メチルスチレン系樹脂
よりも優れた耐熱性を有する重合体が求められている。Furthermore, in recent years, demands for heat resistance for styrenic resins have become higher and higher, and polymers having better heat resistance than α-methylstyrene resins are being sought.
本発明者らは、かかる問題点に鑑み鋭意研究Ｌり＋１ｉ
ｉ４．スチレン、α−アルキルスチレンおよびフレイミ
ド系化合物を特定比率にて共重合させることにより、耐
熱性ならびに流動性に優れる共重合体が得られることを
見出し本発明に到達したものでおる。In view of these problems, the present inventors have conducted extensive research.
i4. The present invention was achieved by discovering that a copolymer with excellent heat resistance and fluidity can be obtained by copolymerizing styrene, α-alkylstyrene, and a flamide compound at a specific ratio.
本発明は、スチレン（ａ−１）２０〜９５ＪＩＦ量チと
α−アルキルスチレン（ａ−２）８０〜５ｉ１ｆｔ％か
らなる芳香族ビニル化合物（Ａ）３０〜９８Ｒ量チとマ
レイミド系化合物（Ｂ）７０〜２Ｎ量チとを共重合させ
ることを特徴とする耐熱性ならびに流動性に優れる共重
合体の製造法を提供するものである。The present invention comprises an aromatic vinyl compound (A) consisting of 20 to 95 JIF of styrene (a-1), 80 to 1 ft% of α-alkylstyrene (a-2), and a maleimide compound (B) of 30 to 98 R. The object of the present invention is to provide a method for producing a copolymer having excellent heat resistance and fluidity, which is characterized by copolymerizing a 70 to 2 N amount of a copolymer.
〈発明の構成〉
本発明において用いられる芳香族ビニル化合物（Ｎとマ
レイミド系化合物ω）との重量比率は芳香族ビニル化合
物（Ａ）３０〜９８重ｔ％、マレイミド系化合物（Ｂ）
７０〜２Ｎ量チである。芳香族ビニル化合物（Ａ）が３
０重量％未満では流動性に劣り、一方マレイミド系化合
物（Ｂ）が２重量ｔ％未満では耐熱性に劣り好ましくな
い。耐熱性ならびに流動性のバランス面より芳香族ビニ
ル化合物（Ａ）４０〜９５Ｎｉｉ％、マレイミド系化合
物中）６０〜５′Ｎ量チであることが好ましい。<Structure of the Invention> The weight ratio of the aromatic vinyl compound (N and maleimide compound ω) used in the present invention is 30 to 98 wt% for the aromatic vinyl compound (A) and 30 to 98 wt% for the maleimide compound (B).
The amount is 70-2N. Aromatic vinyl compound (A) is 3
If the amount of the maleimide compound (B) is less than 0% by weight, the fluidity will be poor, while if the amount of the maleimide compound (B) is less than 2% by weight, the heat resistance will be poor, which is not preferable. In view of the balance between heat resistance and fluidity, it is preferable that the aromatic vinyl compound (A) be 40 to 95 Nii% and the maleimide compound (A) be 60 to 5'N.
本発明の芳香族ビニル−マレイミド系共重合体を製造す
るにおいて特に重要な点は、芳香族ビニル化合物（Ａ）
が、スチレン９５〜２０！ｉ１％、α−アルキルスチレ
ン５・−８０］［３１％であることである。A particularly important point in producing the aromatic vinyl-maleimide copolymer of the present invention is that the aromatic vinyl compound (A)
However, styrene is 95-20! i1%, α-alkylstyrene 5·-80][31%.
芳香族ビニル化合物（Ｎに占めるスチレン量が２０重童
チ未満では流動性が劣り、一方、α−アルキルスチレン
が５１：ｔ％未満では耐熱性に劣シ好ましくない。If the amount of styrene in the aromatic vinyl compound (N) is less than 20%, the fluidity will be poor, while if the amount of α-alkylstyrene is less than 51:t%, the heat resistance will be poor, which is not preferred.
耐熱性ならびに流動性の面より、特に芳香族ビニル化合
物囚に占めるスチレンが９０〜３０重量％、α−アルキ
ルスチレン１０〜７Ｏｆｉ量係が好ましい。From the viewpoint of heat resistance and fluidity, it is particularly preferable that the aromatic vinyl compound contains styrene in an amount of 90 to 30% by weight and α-alkylstyrene in an amount of 10 to 7Ofi.
なお、共重合体の固有粘度には特に制限はないが、共重
合体の耐熱性ならびに流動性の面より、３０℃、ジメチ
ルホルムアミド溶液における固有粘度が０．３〜１．５
であることが好ましい。There is no particular limit to the intrinsic viscosity of the copolymer, but from the viewpoint of heat resistance and fluidity of the copolymer, the intrinsic viscosity in dimethylformamide solution at 30°C is 0.3 to 1.5.
It is preferable that
α−アルキルスチレンとしては、α−メチルスチレン、
α−エチルスチレン、核アルキル置換α−メチルスチレ
ン、核ハロゲン置換α−メチルスチレンなどが挙げられ
、一種又は二種以上用いることができる。特にα−メチ
ルスチレンが好ましい。As α-alkylstyrene, α-methylstyrene,
Examples include α-ethylstyrene, nuclear alkyl-substituted α-methylstyrene, and nuclear halogen-substituted α-methylstyrene, and one or more types can be used. Particularly preferred is α-methylstyrene.
マレイミド系化合物としては、マレイミド、Ｎ−メチル
７レイミド、Ｎ−エチルマレイミド、Ｎ−フェニルマレ
イミド、Ｎ−０−メチルフェニルマレイミド、Ｎ−０−
エチルフェニルマレイミド、Ｎ−０−クロルフェニルル
イミドなどが挙げられ、一種又は二種以上用いることが
できる。特にＮ−フェニルフレイミド単独又ハＮ−７エ
ニルマレイミドが５０重童チ以上を占めるＮ−フェニル
マレイミドと他マレイミドとの混合物が好ましい。Maleimide compounds include maleimide, N-methyl 7-reimide, N-ethylmaleimide, N-phenylmaleimide, N-0-methylphenylmaleimide, N-0-
Examples include ethyl phenylmaleimide and N-0-chlorophenylimide, and one or more types can be used. Particularly preferred is N-phenylfreimide alone or a mixture of N-phenylmaleimide and other maleimides in which N-7enylmaleimide accounts for 50 or more units.
共重合体は、通常の懸濁重合法、乳化重合法、塊状重合
法、溶液重合法およびそれらの組合せの重合法ＫＪ：り
重合することができ、又、その重合法に適した重合温度
ならひに重合開始剤などの助剤を用いることができる。The copolymer can be polymerized by a conventional suspension polymerization method, emulsion polymerization method, bulk polymerization method, solution polymerization method, or a combination thereof, and at a polymerization temperature suitable for the polymerization method. Auxiliary agents such as polymerization initiators can be used.
さらに、スチレン、α−アルキルスチレンおよびマレイ
ミド系化合物の重合系への仕込み順序には何ら制限はな
く、重合前の一括仕込みはもとより、一部の化合物を仕
込んだ後、重合反応の速度に応じて残量の化合物を断続
的又は連続的に仕込んでもよい。Furthermore, there are no restrictions on the order in which styrene, α-alkylstyrene, and maleimide compounds are charged into the polymerization system; they can be charged all at once before polymerization, or after some of the compounds have been charged, depending on the speed of the polymerization reaction. The remaining amount of the compound may be fed intermittently or continuously.
本発明により得られた共重合体に対し、染顔料、酸化防
止剤、紫外線吸収剤、滑剤、帯電防止剤、充填剤などの
添加剤はもちろんのこと、ＡＢＳ樹脂、アクリロニトリ
ル−スチレン共重合体、ポリスルホン、ポリカーボネー
ト、ポリアミドなどの他の重合体を配合することもでき
る０
本発明について、実施例および比較例に工ってさらに詳
しく説明する。なお部数お工ひチは、重量部および重量
％を示す。In addition to additives such as dyes and pigments, antioxidants, ultraviolet absorbers, lubricants, antistatic agents, and fillers, the copolymer obtained according to the present invention may also contain ABS resin, acrylonitrile-styrene copolymer, Other polymers such as polysulfone, polycarbonate, polyamide, etc. may also be blended.The present invention will be explained in more detail with reference to Examples and Comparative Examples. Note that the number of copies indicates parts by weight and weight %.
実施例１
攪拌機を備えた反応器に脱イオン水１２０部、ラウリル
サルフェートナトリウム塩（乳化剤）１５部、スチレン
５０部、α−１メチルスチレン２０部、Ｎ−フェニルマ
レイミド３０部、過硫酸カリウム（開始剤）０．３部お
工びｔ−ドデシルメルカプタン（分子量調整剤）０．２
部を一括仕込み、６６℃に昇温して重合を行った。重合
転化率は９８％であった。重合後、硫酸１グネシウムに
て塩析し、粉末状共重合体（Ａ）を得た。Example 1 In a reactor equipped with a stirrer, 120 parts of deionized water, 15 parts of sodium lauryl sulfate salt (emulsifier), 50 parts of styrene, 20 parts of α-1 methylstyrene, 30 parts of N-phenylmaleimide, potassium persulfate (starting agent) 0.3 parts t-dodecyl mercaptan (molecular weight regulator) 0.2
The mixture was charged at once and the temperature was raised to 66°C to carry out polymerization. The polymerization conversion rate was 98%. After the polymerization, salting out was performed with 1 gnesium sulfate to obtain a powdery copolymer (A).
共重合体のガラス転位点は１５４℃であり、高化式フロ
ーテスター（２３０℃、６０汀／Ｃ−）による流動量は
、０．７０ ｃｃ／ｍｉｎ であった。The glass transition point of the copolymer was 154°C, and the flow rate measured using a Koka type flow tester (230°C, 60 cm/C) was 0.70 cc/min.
実施例２
実施例１と同様の反応器に、脱イオン水１２０部とラウ
リルサルフェートナトリウム塩２部を仕込んだ後、スチ
レン３０部、α−メチルスチレン５０部、Ｎ−フェニル
マレイミド１５部およびＮ−０−クロルフェニルマレイ
ミド５部からなる混合物の１０％および過硫酸カリウム
０．０３部を仕込み、７０℃に昇温しで重合を開始した
。重合開始後、混合物の残量（９０％）および過硫酸カ
リウム０１２７部を４時間に亘り、連続添加した〇連続
添加終了後、８０℃で２時間維持した。重合転化率は９
８％であった。実施例１同様の処理にエリ粉末状共重合
体Ｂを得た。Example 2 A reactor similar to Example 1 was charged with 120 parts of deionized water and 2 parts of sodium lauryl sulfate, and then 30 parts of styrene, 50 parts of α-methylstyrene, 15 parts of N-phenylmaleimide, and N- 10% of a mixture consisting of 5 parts of 0-chlorophenylmaleimide and 0.03 part of potassium persulfate were charged, and the temperature was raised to 70°C to initiate polymerization. After the start of polymerization, the remaining amount of the mixture (90%) and 0127 parts of potassium persulfate were continuously added over 4 hours. After the continuous addition was completed, the mixture was maintained at 80° C. for 2 hours. Polymerization conversion rate is 9
It was 8%. Eri powder copolymer B was obtained by the same treatment as in Example 1.
共重合体Ｂのガラス転移点は、１５５℃および流動量（
２３０℃、６ｏＨ／ｃａ）は、’０． ｓ ２ ｃｅ／
ｍｉｎであった。The glass transition point of copolymer B is 155°C and the flow rate (
230°C, 6oH/ca) is '0. s 2 ce/
It was min.
実施例３
実施例１と同様の反応器に、脱イオン水１１０部、ドデ
シルベンゼンスルホン酸ナトリウム（乳化剤）２部お工
びα−メチルスチレン２ｏ部を仕込んだ後、７０℃に昇
温。その後過硫酸アンモニウム（開始剤） ０．２５部
全量、ｔ−ドデシルメルカプタン０．１５部全量、およ
びスチレン４０部とＮ−７工ニルマレイミド４０部から
なる混合物の１０％を仕込み１合を開始した。重合開始
後、４時間に亘り混合物の残量（９０％）を連続添加し
実施例１と同様の処理に工り粉末状共重合体Ｃを得た。Example 3 A reactor similar to Example 1 was charged with 110 parts of deionized water, 2 parts of sodium dodecylbenzenesulfonate (emulsifier), and 20 parts of α-methylstyrene, and then the temperature was raised to 70°C. Thereafter, a total of 0.25 parts of ammonium persulfate (initiator), a total of 0.15 parts of t-dodecylmercaptan, and 10% of a mixture consisting of 40 parts of styrene and 40 parts of N-7-enylmaleimide were added to start the first batch. After the start of polymerization, the remaining amount (90%) of the mixture was continuously added over 4 hours, and the same treatment as in Example 1 was carried out to obtain a powdery copolymer C.
共重合体Ｃのガラス転位点は１７１℃であり、流動量（
２３０℃、６ｏ＃／ｉ）は０．２１ ｃｃ／ｍｉｎであ
った０
実施例４
実施例１と同様の反応器へ、脱イオン水１５０部、ヒド
ロキシプロピルメチルセルロース（懸濁剤） ０．２
部、ラウロイルパーオキサイド（開始剤）０．２部、ｎ
−ドデシルメルカプタン（分子量調整剤） ０．２５部
、α−メチルスチレン３０部の８０チお工びＮ−７工ニ
ルマレイミド２５部の５０％を仕込み、７０℃に昇温し
で重合を開始した。重合開始後、α−メチルスチレンの
残部（３０部の十
２０％）Ｎ−フェニルマレイミドの残ｇ（２５部の５０
％）お工ひスチレン４５部を３時間に亘って連続添加し
た。連続添加終了後、さらに８０℃で２時間維持した。The glass transition point of copolymer C is 171°C, and the flow rate (
Example 4 To a reactor similar to Example 1, 150 parts of deionized water, 0.2 parts of hydroxypropyl methylcellulose (suspending agent)
parts, lauroyl peroxide (initiator) 0.2 parts, n
-0.25 parts of dodecyl mercaptan (molecular weight regulator), 50% of 25 parts of 80% N-7 engineered nylmaleimide, 30 parts of α-methylstyrene, and the temperature were raised to 70°C to start polymerization. . After starting the polymerization, the remainder of α-methylstyrene (30 parts, 20%) and the remainder of N-phenylmaleimide (25 parts, 50%) were added.
%) 45 parts of refined styrene was continuously added over 3 hours. After the continuous addition was completed, the temperature was further maintained at 80°C for 2 hours.
′Ｎ会転化率は９５％であった。その後１３０℃でスチ
ームストリッピングを行い、残留モノマーを除去した。'N conversion rate was 95%. Thereafter, steam stripping was performed at 130°C to remove residual monomers.
口過、水洗、乾燥し、ビーズ状共重合体りを得た。The mixture was filtered, washed with water, and dried to obtain a bead-like copolymer.
共重合体りのガラス転位点は１４７℃であり、流動量（
２３０℃、６１１１Ａ９／ｉ）は０．８５ ｃｃ／１ｎ
ｉｎであった。The glass transition point of the copolymer is 147°C, and the flow rate (
230℃, 6111A9/i) is 0.85 cc/1n
It was in.
比較例１
実施例１におけるスチレン５０部お工びα−メチルスチ
レン２０部をスチレン７０部およびα−メチルスチレン
０部に変更し、実施例１と同様にして重合し、スチレン
−Ｎ−７工ニルルイミド共重会体を得た。重合転化率は
９８チであった。Comparative Example 1 50 parts of styrene and 20 parts of α-methylstyrene in Example 1 were changed to 70 parts of styrene and 0 parts of α-methylstyrene, polymerization was carried out in the same manner as in Example 1, and styrene-N-7 A nyllimide copolymer was obtained. The polymerization conversion rate was 98%.
共重合体のガラス転位点は１４０℃であり、流動量（２
３０℃、６０Ａ９／ｉ）は０．８９ ｃｃ／１ｎｉｎで
あった。The glass transition point of the copolymer is 140°C, and the flow rate (2
30° C., 60A9/i) was 0.89 cc/1 nin.
比較例２
実施例２におけるスチレン４０部およびα−メチルスチ
レン４０部をスチレン８部お工びα−メチルスチレン７
２部に変更し、実施例２と同様にして１合し、共重合体
を得た。重合転化率は８７量（２３０℃、６０＃／ｃＷ
１）は０．２４ ｃｃ／ ｍｉｎであった。Comparative Example 2 40 parts of styrene and 40 parts of α-methylstyrene in Example 2 were mixed with 8 parts of styrene to obtain 7 parts of α-methylstyrene.
The mixture was changed to 2 parts and combined in the same manner as in Example 2 to obtain a copolymer. The polymerization conversion rate was 87% (230°C, 60#/cW
1) was 0.24 cc/min.
〈発明の効果〉
芳香族ビニル化合物とマレイミド化分物とからなる共重
合体において、芳香族ビニル出会物として特定比率にて
スチレンとα−アルキルスチレンを用いることにより、
耐熱性ならびに流動性に優れる共重合体を、効率よく（
未反応体が少ない）製造することが可能である。<Effect of the invention> In a copolymer consisting of an aromatic vinyl compound and a maleimide compound, by using styrene and α-alkylstyrene in a specific ratio as aromatic vinyl encounters,
Copolymers with excellent heat resistance and fluidity are efficiently produced (
(with less unreacted substances).
Claims (1)
チレン（ａ−２）８０〜５重量％からなる芳香族ビニル
化合物（Ａ）３０〜９８重量％とマレイミド系化合物（
Ｂ）７０〜２重量％とを共重合させることを特徴とする
耐熱性ならびに流動性に優れる共重合体の製造法。30-98% by weight of an aromatic vinyl compound (A) consisting of 20-95% by weight of styrene (a-1) and 80-5% by weight of α-alkylstyrene (a-2) and a maleimide compound (
B) A method for producing a copolymer with excellent heat resistance and fluidity, characterized by copolymerizing 70 to 2% by weight.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP369085A JPS61162507A (en) | 1985-01-11 | 1985-01-11 | Production of copolymer with high heat resistance and good flowability |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP369085A JPS61162507A (en) | 1985-01-11 | 1985-01-11 | Production of copolymer with high heat resistance and good flowability |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS61162507A true JPS61162507A (en) | 1986-07-23 |
Family
ID=11564390
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP369085A Pending JPS61162507A (en) | 1985-01-11 | 1985-01-11 | Production of copolymer with high heat resistance and good flowability |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61162507A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6236442A (en) * | 1985-08-09 | 1987-02-17 | Japan Synthetic Rubber Co Ltd | Heat-resistant resin composition |
| JPS63182309A (en) * | 1987-01-22 | 1988-07-27 | Ube Saikon Kk | Production of thermoplastic heat-resistant resin |
| JP2009102495A (en) * | 2007-10-23 | 2009-05-14 | Tosoh Corp | Method for producing polymer |
| WO2009107765A1 (en) * | 2008-02-28 | 2009-09-03 | 東レ株式会社 | Process for production of thermoplastic copolymer |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5667317A (en) * | 1979-11-07 | 1981-06-06 | Denki Kagaku Kogyo Kk | Production of thermoplastic resin |
| JPS5698210A (en) * | 1979-12-21 | 1981-08-07 | Ici Ltd | Manufacture of polymer particle and coating composition containing said particle |
| JPS58162616A (en) * | 1982-03-24 | 1983-09-27 | Toray Ind Inc | Production of maleimide copolymer |
-
1985
- 1985-01-11 JP JP369085A patent/JPS61162507A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5667317A (en) * | 1979-11-07 | 1981-06-06 | Denki Kagaku Kogyo Kk | Production of thermoplastic resin |
| JPS5698210A (en) * | 1979-12-21 | 1981-08-07 | Ici Ltd | Manufacture of polymer particle and coating composition containing said particle |
| JPS58162616A (en) * | 1982-03-24 | 1983-09-27 | Toray Ind Inc | Production of maleimide copolymer |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6236442A (en) * | 1985-08-09 | 1987-02-17 | Japan Synthetic Rubber Co Ltd | Heat-resistant resin composition |
| JPS63182309A (en) * | 1987-01-22 | 1988-07-27 | Ube Saikon Kk | Production of thermoplastic heat-resistant resin |
| JP2009102495A (en) * | 2007-10-23 | 2009-05-14 | Tosoh Corp | Method for producing polymer |
| WO2009107765A1 (en) * | 2008-02-28 | 2009-09-03 | 東レ株式会社 | Process for production of thermoplastic copolymer |
| JPWO2009107765A1 (en) * | 2008-02-28 | 2011-07-07 | 東レ株式会社 | Method for producing thermoplastic copolymer |
| US8258244B2 (en) | 2008-02-28 | 2012-09-04 | Toray Industries, Inc | Process for production of thermoplastic copolymer |
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